Fabric softener



United States Patent 3,505,221 FABRIC SOFTENER Milton M. Waldman, Northbrook, and Andrea E. Mariahazy, Westchester, Ill., assignors, by mesne assignments, to Armour Industrial Chemical Company, a corporation of Delaware No Drawing. Continuatiou-in-part of application Ser. No. 566,471, July 20, 1966. This application June 9, 1967, Ser. No. 644,819

Int. Cl. D06m 13/46; C07c 87/30; Clld 3/30 US. Cl. 252-8.75 3 Claims ABSTRACT OF THE DISCLOSURE A fabric softener comprising certain arylalkyl quarternary compounds useful in either the wash or the rinse waters during the laundering of fabric.

This application is a continuation-in-part of application Ser. No. 566,471, filed July 20, 1966, now abandoned.

This invention relates to novel fabric softener compositions and methods for their use, and more particularly to compositions which, when applied via the wash or rinse waters during laundering of fabric, uniquely impart softening characteristics without the customary deleterious effect on the rewet characteristics of said fabric.

In the past, fabric softeners, which render fabric soft to hand feel and touch upon drying, after laundering, especially with detergent, comprised di-higher alkyl quaternary ammonium compounds. Where the compound contained only one long chain, its softening abilities were not as pronounced, and in many instances were totally absent in subjective testing.

Usually, the fabric softener was added to the rinse water because of incompatability with the detergents, and so that it would be retained by the fabric upon drying. Recent developments have uncovered softener compounds which may even be added to the wash water. They uniquely possess a substantivity to the fabric which is not deleteriously affected by the detergent of the wash water.

Unfortunately, generally softeners cut the absorbency by water of the fabric. Diapers, towels, drying cloths, underwear, underarm pads, stockings and socks, and the like, which desirably are treated with fabric softener to make them soft to the touch lose their absorbency to moisture because of the softener. The rewet properties are substantially diminished because of the presence of the long chain quaternary softener which seems to impart a wax-like coating on each fiber of the fabric so that rewetting is difiicult.

An object of the invention is to'provide a novel softener composition and method for its use.

Another object of the invention is to provide a softener composition which may be used in the' wash water during laundering.

Still another object is to provide a softener composition which retains good rewet properties by the fabric which has been treated.

A further object is to provide a softener composition which uniquely promotes lint coagulation.

A still further object is to provide a softener composition which also imparts anti-static characteristics espe cially useful with synthetics and wool.

Other objects of the invention will in part be obvious and will in part appear hereinafter.

It has now been found that when certain arylalkyl quaternary compounds are admixed with the wash or rinse waters for fabrics, they impart a unique softening action upon the fabric while retaining the rewet properties 3,505,221 Patented Apr. 7, 1970 of said fabric. In addition, such compounds enhance lint coagulation and act as anti-static agents on said fabric, especially woolen or synthetic fabric. Compounds having the following structure are useful:

FORMULA I where R is a member of the group consisting of CH;,,

CH CH CH CH CH and R is a member of the group consisting of unsubstituted phenyl and phenyl substituted with from 1 to 2 groups selected from methyl, hydroxy, and methoxy;

R and R are each members of the group consisting of CH CH CH CH CH CH and where R is a member of the group consisting of H and CH A is an anion such as a halogen, a nitrate, a nitrite, a

sulfate, an acetate and the like;

n is an integer from 1 to 2;

x and y are integers from 0 to 19 with the total thereof ranging between 5 to 19;

z is an integer from 1 to 40 and where R and R are the total is no greater than 60.

For wash water addition, 0.01 to 0.5% by weight and preferably about 0.2% is desirable, whereas for rinse water addition, 0.01 to 0.5% by weight and preferably about 0.1% is used. The percent by weight of softener is based on the weight of fabric to be treated.

The invention accordingly comprises a composition of matter possessing the characteristics, properties, and the relation of components which will be exemplified in the composition hereinafter described, and the several steps and the relation of one or more of such steps with respect to each of the others thereof, which will be exemplified in the method hereinafter disclosed, and the scope of the invention will be indicated in the claims.

Reference is now made to the following examples which illustrate the composition and the method of use of the compounds of Formula I:

' EXAMPLE I Trimethyl phenyloctadecyl ammonium chloride, trimethyl tolyloctadecyl ammonium chloride, dimethyl di- (phenyloctadecyl) ammonium chloride and trimethyl xylyloctadecyl ammonium chloride show good softening (almost equivalent to Arquad 2HT, which is dimethyl di-tallow quaternary ammonium sold by Armour and Company, Chicago, Ill., and as used in commercially available softeners) when added to the rinse water during washing of Curity (trademark) diapers. However, the softening is of a different nature. It does not have as waxy a hand as with Arquad 2HT.

3 When tested for rewet evaluation by the wicking test, the following results are obtained:

TABLE 1 strip of Curity Diaper material, previously treated with the softener under test, is weighted at one end. The weighted end is immersed /2 inches into dye solution and the top of the strip is clipped to a rod suspended across the top of the graduate. Aluminum foil is used a to seal the top of the graduate to reduce evaporation. A 150 (Avg. 10 runs) softening stop Watch is started at the moment the test strip 18 Softener 5 30 mm Pmpefties immersed in the dye solution. The height of the discolora- Uiitreated 10.9cm 19.0cm tion above the liquid level is measured every 5 to amino pdl lis iirqilad 300mm" Excellent 10 minutes (over a 30 minute period) depending on the rate 2 HT (traditional rewet iormula- Of Wetting. I I 1.332611%-nfiilfifigiyi-afif A plot of height vs. time is made. An untreated blank monjumchloride 1363mm D0 i run and plotted. A control of Arquad 2HT treated Ttimethyl mlyloctadecyl ammo at 0.15% basis cloth is also run. Significant ditierences ium chloride. 9. 7 cm 16.8cm Do. Dimethyldi(phenyloctadecyl) am- 10.8em l9,ficm D0 are considered to be 10% of the maximum diiterence o gifii t l ecyl quaternary 3 0 cm Do between the blank and the control I ammonium chloride. It should be evident from the data in Table 1 that the Trimethyl y ifi y Quilter specifically named arylalkyl quaternary softeners above niin itfifi fifiifihefiifitadec i 13.0cm Do, have better rewet characteristics than the popular citihmi ammmium chmride- 2 mercially used Arquad 2HT softener. The dime y gifi li k i m g u iii 192cm Do 0 di(phenyloctadecyl) ammonium chloride treated diaper ffiggg g (3 moles) pheuy10cta is 50m Fair even has a rewet characteristic as good as the nondecyl methyl ammonium softened diaper while showing good softening. It 1s also chlorideapparent that the quaternaries with an aryl group as 5 compared to Arquad 2HT or other quaternaries without an aryl substituent are substantially better on rewet characteristics. Although the trimethyl octadecyl quaternary has slightly EXAMPLE 11 higher softening properties than the trimethyl xylyloctadecyl quaternary, it is evident from Table 1 that the tri- Addltlonal quaternallfis cgmblflatlons 0f q h l l l d l quaternary i f Superior i h names were evaluated using Tide' by Protcter& Gamble respect to rewet, The presence of the aryl group ap- Of Cincinnati, 01110, b6 laundering detergent as fOlparently has caused improved rewet characteristics. lows:

TABLE 2 Softening Rewet (Avg. 10 Runs) Parts by Rinse 0.1% 1 Wash 0.2% 1 Softener Weight 5 min. 30 min. Added Added Untreated 10. 9 19. 0 Dimethyl di-tallow ammonium chloride 2. 7 5. 4 Excellent. Dimethyl di(phenyloctadecy1) ammonium chloride 11. 1 21. 0 Acceptable Digital: softer treated.

Dimethyl di(phenyl0ctadeeyl) ammonium chloride 1 4 3 Dimethyl di tallow ammonium chloride 1 Dimethyl di(phenyloctadecyl) ammonium chloride 1 4. 3 Arquad 2HT 3 Trimethyl phenylootadecyl ammonium chloride- Trimethyl xylyloetadecyl ammonium chloride Trimcthyl plienyloctadecyl ammonium chloride. Arquad 2HT Trimethyl phenyloctadecyl ammonium chloride, Arquad 2HT Tiimethyl xylyloctadeeyl ammonium chloride Arquad 2HT Trimethyl xylyloctadecyl ammonium chloride Arquad 2HT Trimethyl tolyloct-adecyl ammonium chloride Trimethyl hydroxyphenyloetadecyl ammonium chloride Trimethyl hydroxyphenyloctadecyl ammonium chloride Arquad 2HT Trimethyl tolyltallow ammonium chloride 'lrimethyl tolyloctadecyl ammonium chloride Arquad 2HT Trimethyl tolyloctadecyl ammonium chloride Arquad 2HT Trirnethyl tolyloctadecyl ammonium chloride Arquad 2HT Trimethyl tolyloctadecyl ammonium chloride Arquad 2HT Diniethyl dittolyloctadecyl) ammonium chloride Dimethyl di(tclyloctadecyl) ammonium chloride Arquad 2HT Dimethyl dittolyloctadecyl) ammonium chloride Arquad 2HT Heudecylphenyl ammonium chloride Phenylbehenic ammonium chloride Ethoxylated (2 moles) di(phenyloct-adecyl) methyl ammonium chloride. Arquad 2HT 1 Based on weight of fabric.

Wicking Test Material:

1 liter graduate Kiton Red 26 DyeCIBA Curity diaper Procedure.-Into a 1 liter graduate, pour 200 ml. of

Excellent Do. Acceptable Fain Excellent Acceptable Good Excellent I Acceptable.

Fair

8. 5 Good Fair The di(phenyloctadecyl) and di(tolyloctadecyl) ammonium chloride, when used in the wash cycle, show a unique agglomeration of lint into discrete hard particles which can be more easily removed from the lint filter.

EXAMPLE III Softener compositions utilizing certain di-phenyl quatera a 0 so u on of l lon Red 26 Dy A 15 nch wide c ries are formu ated and then evaluated q l a iv ly y a panel of housewives and the following test results are obtained:

'IA BL E 3 Softening 1 Wash Added, Parts Percent by Preter- Soitener Composition Wt. once Untreated L 31. Dimethyl di(phenyloctadecyl) ammonium chloride... 75 68 4 Dimethyl ditallow ammonium chloride 25 Dimethyl d i(phenylootadecyl) ammonium cholride.-. 1 64 6 Dimethyl ditallow ammoniurn'chloride 1 Dimethyl di(phenyloctadecyl) ammonium chloride 25 84 1 Dimethyl ditallow ammonium chloride 75 Dimethyl di(phenyloetadecyl) ammonium ehloride 75 61 8 Armosoit D O 2 25 Dimethyl di(phenyloctadecyl) ammonium chloride..- 1 47 2 Armosoit DC 3 1 Dimethyl d.i(phenyloctadecyl) ammonium chlori 25 44 6 Armosoft DC 2 75 1 0.2% on wt. of fabric. reivfgtrmosoit DC=au Arquad 2HT type softener modified to improve It should be evident from the above examples that a substantial improvement in the fabric softening art has been accomplished. Now, softening as well as maintenance of rewettability is retained. Surprisingly, lint coagulation is also accomplished.

It might be noted that the di-xylyl and the di-tolyl substituted quaternaries appear to be the most elfective, so these are preferred.

In selling softener formulations to the consumer, an aqueous concentrate of 1 to 20% by weight of the softener is generally utilized. Similar formulations for the softener of this invention may also be utilized for retail sale.

It will thus be seen that the objects set forth above, among those made apparent from the preceding description, are efiiciently attained, and, since certain changes may be made in the above composition of matter and in carrying out the above method without departing from the scope of the invention, it is intended that all matter contained in the above description shall be interpreted as illustrative and not in a limiting sense.

It is also to be understood that the following claims are intended to cover all of the generic and specific features of the invention herein described, and all statements of the scope of the invention, which, as a matter of language, might be said to fall therebetween.

We claim:

1. A softener composition consisting essentiall of an aqueous solution of l to 20% by weight of an arylalkyl quaternary falling within the following formula:

where R is a member of the group consisting of CH;;-,

CH CH CH CH CH and R is a member of the group consisting of unsubstituted phenyl and phenyl substituted with from 1 to 2. groups selected from methyl, hydroxy, and methoxy;

R and R are each members of the group consisting of CH;;-, CH CH CH CH CH and where R is a member of the group consisting of H and CH A is an anion such as a halogen, a nitrate, a nitrite, a sulfate, an acetate;

n is an integer from 1 to 2;

6 x and y are integers from 0 to 19 with the total thereof ranging between 5 to 19; z is an integer from from 1 to 40 and where R and R are H(O(!3HCHz)| radicals, the total is no greater than 60.

2. A rinse Water for laundered fabric consisting essentially of about 0.01 to 0.5% by Weight of the fabric being washed of an arylalkyl quaternary falling within the following formula:

R1 n[CH (CHz)+lCH(CH2) CHzl}I-R ]+A"() where:

R is a member of the group consisting of CH;,,

CH CH CH CH CH and CH3(OH2)x'(])H (CH2)yCHL R is a member of the group consisting of unsubstituted phenyl and phenyl substituted with from 1 to 2 groups selected from methyl, hydroxyl, and methoxy; R and R are each members of the group consisting of CH3', CH3CH2, CH3CH2CH2- and 11 0 TJHCHQF where R is a member of the group consisting of H and CH A is an anion such as a halogen, a nitrate, a nitrite, a

sulfate, an acetate; n is an integer from 1 to 2; x and y are integers from 0 to 19 with the total thereof ranging between 5 to 19; z is an integer from 1 to 40 and where R and R are H(O (|JHCH2)= radicals, the total is no greater than 60. 3. A method for softening fabric comprising adding 0.01 to 0.5% by weight of the fabric of an arylalkyl quaternary falling within the following formula:

R is a member of the group consisting of CH CH CH CH CH CH CH CH and R is a member of the group consisting of unsubstituted phenyl and phenyl substituted with 1 to 2 groups selected from methyl, hydroxy, and methoxy;

R and R are each members of the group consisting of CH;;., CH3CH2-, and

where R is a member of the group consisting of H and CH A is an anion such as a halogen, a nitrate, a nitrite, a sulfate, an acetate;

n is an integer from 1 to 2;

x and y are integers from 0 to 19 with the total thereof ranging between 5 to 19;

7 8 z is an integer from 1 to 40 and where R and R are 3,274,106 9/ 1966 Smiens 2S28.75 Hm CHCHZ) 3,296,145 1/1967 Findlan et a1. 252106 1 3,351,483 11/1967 Miner et a1. 117-66 3,360,470 12/1967 Wixon 252-99 radicals, the total is no greater than 60;

5 to water and immersing said fabric therein. HERBERT GUYNN Pnmary Exammer D. L. ALBRECHT, Assistant Examiner References Clted UNITED STATES PATENTS US. Cl. X.R. 2,746,928 6/1952 Darragh et a1 252--106 117 139.s; 2528.8, 152; 260-5675 

